Crystal structure and hydrogen bonding in the hydrated cocrystalline salt tryptaminium–3, 5‐dinitrobenzoate–quinoline–water (3/3/2/2). Issue 10 (23rd September 2016)

• Record Type: Journal Article
• Authors: Lynch, Daniel E.; Smith, Graham; Keene, Tony D.; Horton, Peter N.
• Is Part Of: Acta crystallographica. Volume 72:Issue 10(2016)
• Page Start: 738
• Page End: 742
• Publication Date: 2016-09-23
• Subjects: ternary crystal structures -- tryptamine salts -- molecular adducts -- 3, 5‐dinitrobenzoic acid -- quinoline adduct -- hydrogen bonding -- π–π interactions -- solid‐state organic chemistry; Crystallography -- Periodicals; Crystals -- Periodicals; 548.3
• DOI: 10.1107/S2053229616014728
• Languages: English
• ISSNs: 2053-2296

Abstract

Abstract : The crystal structure of the bis(quinoline) adduct dihydrate of tris(tryptaminium 3, 5‐dinitrobenzoate) shows an extensively hydrogen‐bonded and π–π‐bonded one‐dimensional columnar extension. Abstract : The study of ternary systems is interesting because it introduces the concept of molecular preference/competition into the system where one molecule may be displaced because the association between the other two is significantly stronger. Current definitions of a tertiary system indicate that solvent molecules are excluded from the molecule count of the system and some of the latest definitions state that any molecule that is not a solid in the parent form at room temperature should also be excluded from the molecule count. In the structure of the quinoline adduct hydrate of tryptaminium 3, 5‐dinitrobenzoate, 3C10 H13 N2 + ·3C7 H3 N2 O6 − ·2C9 H7 N·2H2 O, the asymmetric unit comprises multiple cation and anion species which are conformationally similar among each type set. In the crystal, a one‐dimensional hydrogen‐bonded supramolecular structure is generated through extensive intra‐ and inter‐unit aminium N—H…O and N—H…N, and water O—H…O hydrogen bonds. Within the central‐core hydrogen‐bonding associations, conjoined cyclic R 4 4 (10), R 5 3 (10) and R 4 4 (12) motifs are generated. The unit is expanded into a one‐dimensional column‐like polymer extending along [010]. Present also in the crystal packing of the structure are a total of 19 π–π interactions involving both cation, anion and quinoline species [ring‐centroid separation range = 3.395 (3)–3.797 (3) Å], as well as a number of weak C—H…O hydrogen‐bonding associations. The presence of the two water molecules in the crystal structure is considered to be the principal causative factor in the low symmetry of the asymmetric unit.